The Neverending RoadTrip
by Bernadette Pretlow
Summary: Sam and Dean are on the road again when they find another case. In comes Kiara a girl on the run, she needs to escape from her past, and meets Castiel her angel in disguise. When they all meet together chaos ensues... as per the norm.
1. Chapter 1

**HI EVERYONE I JUST WANT TO SAY THIS IS MY FIRST EVER FANFIC. PLEASE REVIEW OR RATE OR FAV. I WANT TO WRITE MORE, BUT I CAN'T IMPROVE UNLESS I GET CRITIQUES SO CRITIQUE ME!**

 ******DISCLAIMER: I DO NOT OWN SUPERNATURAL OR ANY OF THEIR CHARACTERS************

Sam didn't like clowns. He hated them, ever since they tried to make a balloon animal shaped like his dead dog he cringes in fear. Which is why this trip was his least favorite.

"Hey Sam check this out" said Dean as he scooted the newspaper over the table. They were at their regular diner in Kansas "Shelly's"; only in town to pay respects to their mother and then be on their way. The article was about a boy that had died of a seizure after clowns came to his birthday party. Sam wasn't amused.

He glared at Dean, "Real funny Dean" he said.

"hehehe" Dean chuckled as he went through the papers to find some new case for them. When he came across an article "Kids 'N Instagram: A Suicidal Case?" The article talked about how an above average number of students were committing suicide the more glamorous their lives seemed on the internet the less it was in real life. Dean passed the article to Sam.

"What do you think this is?" Dean asked. Sam surveyed the article and then looked up grimly at Dean.

"I think it's our next case."


	2. Visiting Uni Kiara's escape

**DISCLAIMER I DO NOT OWN SUPERNATURAL OR ANY OF THESE CHARACTERS**

Sam and Dean approached Kansas State University in Dean's Impala. As Dean parked the car they surveyed the campus. Practically a scene from any college movie; sorority girls flirting with frat guys. People sitting in the quad chilling. Compared to their rather hectic life this seemed rather quiet and peaceful.

"So this is college," said Dean as he got out of the car. "Well better late than never" he exclaimed as some sorority girls passed him by and winked at him.

"Dude seriously?" Sam asked. "There are like a million things we have to do here there's no time to flirt with anyone, so cool it Casanova."

Dean eyed Sam rather suspiciously. Dean knew how to act professionally (most of the time) but he was known to drop a joke or be the first one to hit on a cute girl. What was going on with Sam?

"Casanova? Come on man, look at all these chicks! Ughh if I was a frat guy..." Sam glared at Dean "Right, so where should we start College Man?" asked Dean.

"The last student was Alexis Holster, Freshman, marine biology major, lived in a sorority house." said Sam as he looked through the file they had confiscated from the police files online.

"What happened was she tired of the awesome partying?" Dean asked. At this point Sam just didn't reply he just shook his head and went to find the sorority house that Alexis lived in. Leaving Dean dumbfounded and frustrated that Sam was leaving him like that.

Kiara was running as fast as she could. Gambling was the name of the game recently, and boy was she really gambling. In the past five years she had gambled her way through life, through foster care, high school, and now with other people's lives.

She had never thought that her mother's ancient taboo cards would cause such a ruckus in such a small town. She was somewhere outside of Kansas City and needed out needed a new identity so that no one will remember her. They can't remember her, and she needs to forget.

It was already dark when she runs past a 7 Eleven and starts to get tired and cramped, with nowhere to go without fatigue she decides to hotwire a car. From the minimal selection of the 7 Eleven she's got a Chevy Impala, a Honda, and a fiat.

"I mean Chevy was always my favorite brand" she whispered to herself as she sneaked her way through the gas pumps and behind the car; checked to see if there was anybody in there and when the coast was clear she used a bobby pin to open the car and began playing with the wires to be able to jumpstart the car.

Once she was able to start the car however the owners of the Chevy came out of the 7 Eleven and couldn't believe that their car was being stolen. They shouted and threatened death if Kiara didn't come back with their car.

"Sorry boys, Mama needs to amscray out of here, now let's see," she said as she was rummaging through the car. She finds pamphlets for New York and Canada.

"hmm, I hear the bacon is good there" she gets so distracted by the pamphlets that she doesn't realize she's run a red light. horns blare in the distance and she focuses back on the road. "idjits." she whispers to herself, as she drives off.

 **SO I THINK I'M GONNA ADD A RELATIONSHIP BETWEEN DEAN AND KIARA IDK HOW TO ADD HER TO THEIR STORY ANY SUGGESTIONS PLEASE RATE AND REVIEW AND TALK TO ME PLEASSSSE.**


	3. Kiara meets Castiel

**disclaimer I DO NOT OWN SUPERNATURAL NONE OF THESE CHARACTERS ARE MINE.**

 **Shout out to Lexiimakay16 for helping me out and reviewing! I appreciate it!**

Kiara had stopped somewhere around Topeka to get gas around 3 am. She pulled in into the abandoned parking lot of an old drive in movie theatre; it was a cold night the stars were out. If she wasn't in such a hurry to escape she would have thought it was quite romantic, but of course that could never be Kiara was destined for a life on the road; her home became wherever she could find where they were serving ice cold beer and a good baseball game. Love for Kiara? Highly unlikely.

As she sat on the hood of the black Chevy Impala she thought of the new characters she would play to get by. Her formula for getting by was simple don't do something noticeable, and don't make friends. Friends just bring unnecessary emotions that she couldn't have in her way of life. She had looked through the pamphlets that the previous owners had left behind : _restaurants, museums, strip club, aquarium, great. Soo many options. Let's see eenie meenie miney moe... and Strip Club it is. Watch out bitches._

She through the pamphlets in the air, and got in her car sped her way through the lonely streets. It was incredible that she was never pulled over for reckless driving because there were just too many hairpin turns in a 15 minute drive to be even considered sane. As she pulled up to the club she could already tell this was going to be one of her worse jobs _I think I prefer working with Flipper_ she thought to herself as she walked into the club.

It looked like something out of a 70's porno the girls were dressed as slutty starlets and the men all seemed to be impersonating someone from Goodfellas. The furniture was completely outdated and it smelled of greasy food and cheap perfume. She pushed up her bra and made her way to the bar.

"Can I see the manager please?" She asked seductively to the 20 something handsome young man behind the bar. He looked at her and blushed then sheepishly went away and a few minutes later came back with an older man probably around 45 or 65. He looked at her up and down in a sexual way and turned to the bartender and said " Castiel you can take your break now". _Castiel what a beautiful name ._

Castiel quickly looked up at Kiara , with the most intense stare ever as if to say that she should leave, almost a warning; and then back at his boss and shyly went away. The man know looked at Kiara with eager eyes and offered her a drink to which she declined, "What can I do for you my dear?" he asked.

" I'd like a job" she said bluntly.

He smiled creepily and Kiara knew what was going to come next, this wasn't her first rodeo. "Well sweetheart, to work here you gotta work _hard_ all my girls give more than just dances, do you think you're okay with that?" he said low.

Kiara slowly walked to the man and took his hand seductively walking him back to his office, " baby I can do anything". She opened the door and they walked in together, she released his hand and closed the door. He was sitting in a chair in front of his desk already sweating from the excitement he had. She turned towards him, sexually walking towards him; sort of a pre lap dance then she straddled on to him and caressed his face, "what do you want me to do baby?" she asked almost in a whisper.

"I want you to screw me" he said exasperatingly. Kiara didn't need to be told anything more, she kissed him first soft and slow then passionate and hard. she started to grind on him to get him hard. He stood up and kept her straddled on him still kissing they slowly made their way to the floor and he started taking off his pants Kiare aggreseviley to off his shirt. "I like the way you play baby"he smirked as she started to stroke his massive erection he let out a gasp. "Oh god yes!" he yelled. Then she started to suck his dick, she'd lick the tip of his cock and gave him nice long strokes. she deep throated his cock until he came in her mouth "ohhhh yes yes yes!" he kept yelling.

As she was giving him a blowjob, he started to take off her shirt and caress her tits. She moaned "hmmmm" he then took off her bra and starting groping her breasts big and voluptuous he grabbed her like a ragdoll and put her on top of him he sucked her breasts and she continued to moan "mhhmmm oooh ahhhh" he slowly made his way down to her clit and started to finger her " I think my customers would love you" he licked her face " I know I do, you're so tight I need to be in you" he took her off him and onto the floor and then put his massive dick into her and started thrusting and thrusting harder and faster " do you like that baby" he asked.

"ohh YES FUUCK ME!" she yelled. With his hands on her breasts he thrusted harder until she came. "Sweetheart you got the job" he said sometime after.

Kiara felt disgusting. This was her life she felt so low and gross. She put her clothes back on and walked out of the office she was almost home free when someone stopped her she could barely make out who it was she was almost on the verge of tears that she didn't want to see anyone. The person was talking to her but she couldn't make out what they were saying all she could hear was her subconscious calling her a slut.

"Hey wait!" she turned around and saw Castiel. Even in light of what happened he looked like an angel. "You shouldn't have gotten a job here"he said. She scoffed and walked out of the club he followed her.

"No seriously listen to me, you seem like a nice girl don't work here. I've seen what happens to people that work here." he pleaded. She stopped and turned around now they were face to face.

"I really need a job and I don't have a high school education, listen why don't you just but out?" She said. "Care about yourself, I can do fine by myself" she turned around and continued walking to her car.

"Wait- I mean, Hey!" he yelled, with a kind of worry in his face. "You have rights you know you didn't have to do what you did back there, I mean I know what this place is but you're better than this" he said pointing to the club. "Listen I just wanted to let you know that I'm here a lot of the other girls in the past found it was easy to come and talk to me about stuff. Don't be a stranger" he said.

"Like I really need your help kid." She stopped herself before she was going to say something she might have regretted, and sighed looked at him for a long moment, "I'm Megan, my friends call me Meg. At least they would if I had any friends."

"Meg" he said

"We're not friends Castiel, we're co workers" she said

"Just know I'm here, this place can get tough; and you don't always have to be" he said

"Thanks" she finally replied as she walked back to her car and drove off to a motel.

Dean was getting worried about Sam something was wrong with him and he wasn't talking about anything. On the ride back to their motel from the University Sam slept and Dean put on the radio Highway to Hell was on. It was a nice day there were no clouds in the sky and everything in their investigation was coming together like it always did. Suddenly as the chorus came on Sam sat up and started speaking Latin.

" Sammy you okay? Hey! Sam come on now don't do this!" Dean was mortified this wasn't Sam he was dealing with.

 **YAAAAAAAS FINALLY DONE WITH THIS CHAPTER IT'S KIND OF A WHATEVER CHAPTER RIGHT NOW IT GOT KIND OF KINKY BUT IT'S A KINKY KIND OF STORY ANYWAYS... AS ALWAYS WOULD LOVE A REVIEW AND YEAHH HAPPY MOTHER'S DAY TO EVERYONE!**


	4. Kiara's First DaySam's Bad Day

**Disclaimer I do not OWN SUPERNATURAL OR ANY OF THEIR CHARACTERS PLEASE REVIEW AND RATE OR JUST TELL SOMEONE. MUCH LOVE -SHARKBAIT**

Dean was beyond worried. Sam had never acted this way; it could have been demon possession they have battled it before. But before they've had Bobby with them.

Dean thought it was a good idea to return back to their home base, and just regroup: _That's what we're doing we're regrouping we just need to -_ _ **CRASH**_ _oh no what now?_ Dean ran out of his room and into the kitchen where Sam had destroyed nearly every furnished furniture, he had a chef's knife in his hand and he wasn't showing the slightest sign of mercy.

"Sam, Sammy buddy calm down. Listen just talk to me what's going on?" Dean said in his super protective rough guy voice, he only ever used if he had to set people straight. Sam turned to look at Dean with a menacing look in his eye he dashed towards Dean

"AAAAARGGGH!" He yelled barbarically. Dean dodged his murder attempt and tried to restrain him, holding him at his wrists making him drop the knife. Sam punched Dean almost breaking his nose. "Sam, don't make me hurt you." Dean pleaded desperately if there was anything that he couldn't bring himself to do is hurting his own brother; he was the only family Dean had left.

"Sam, I know you're in there! You have to fight it Sam, Fight it. Come On!" He was cupping his face ferociously with both of his hands while Sam tried to take his arms and strangle Dean to no avail. After some time it seemed that whatever inner demon Sam was fighting with it was disappearing from his face and from his soul. He looked around all over worried and flustered. Finally he met Dean's eyes. tears were filling his eyes..."Dean, ohh Dean I didn't mean to-" he was cut off by a strong hug by Dean.

"It's okay Sam, it's over now" said Dean as he tried to salvage what's left of their kitchen.

"No Dean it's not. I know there's something wrong with me. And I know that you know about it too."Said Sam. Dean couldn't bear to let Sam down, this was his one job he wasn't going to let him down. He stopped trying to fix the shattered glasses on the floor and stood up, turned to face Sam, "Listen Sammy whatever this is we'll fix it we always do. Don't worry" he tried to say convincingly but Sam always worries.

It was Kiara's first day of work. And she hated herself for working there. She hated herself for what she did to get a job. But tips were good at the clubs and it was only for the moment. _It's always for the moment_

Kiara had been given a real sleazy Sandy from Grease costume. It was a post good girl Sandy towards the end when she wants to get Danny and decides that slutty is the way to get her man. Well there couldn't have been a sluttier girl than Kiara black spanks so tight she could wear underwear a see through tight black boustierre, with cherry red lips, and an excessive amount of hairspray in her hair.

She walked out onto the stage _Good crowd for a Monday_ she thought. There were five different bachelor parties (all VIPS of course), all scattered around the club wearing sleazy outfits throwing bills at the girls that looked less than healthy. With every step she took there were cheers and jeers from the gentlemen in the first row.

"YEAH BABY" said sleazbag #1

"Come on Sweetheart! Let's see them!" said sleazebag #2

Kiara suddenly got nervous but it was something she needed to do and she reminded herself of that _Just remember you need cash_ she thought. Kiara was really good on the pole, she could move her body in ways even she was surprised. To save her identity she used the stage name "Angel's Devil" which if it was a terrible name for any other situation but practically described Kiara to a T.

"Hey Baby you want me to do you right there? hahaha!" said Sleazebag #1

"Nahh Breh you have to do her after me breh" said Sleazebag #2

Kiara finished her routine picked up whatever dignity she left on the floor and left the stage. She passed by the bar for a drink and saw Castiel talking to more bachelors. As she stopped by they all took notice and catcalled her, Castiel told them to back off "This isn't the stage guys she's not gonna do anything for you here." he said seriously.

The guys took their drinks and sat back at their tables, Castiel made sure they were away to turn his full atenttion to Kiara. " How are you holding up?" he asked worriedly.

"I mean, besides the usual harassment calls I've never been better." she said. Casiel cringed and gave her a bottle of water.

"Thanks, on the upside I made $300. Beginner's luck I guess." she said. Castiel looked up at her and tried to fake a smirk but couldn't. He was going to say something else when a customer came up to the bar. "Dry martini please"

"And that's my cue to leave, see ya around" she said as she disappeared backstage.

Castiel served the man his martini and he moved to the table where Kiara's hecklers were annoying her. _I'm gonna quit any day now._

As Kiara came out for a second time her hecklers seemed to be more agitated "Come on baby just let me-" Sleazebag #1 tried to grab heron stage to which she slapped his hand. "Look at that she's a feisty little thing" said sleazebag #2 as he tried to grab her from the other side.

"Y'all better stop!"she exclaimed. she was suddenly very defensive and agitated.

"Now sweetheart we're just having some fun" said the man from the bar. Before Kiara could even turn to face him she heard his gun **click** and shivers ran through her spin. He had a gun to her back "Now you better do as we say sugar" he told her quietly.

Kiara wasn't a stranger to guns she knew how to handle herself in a situation like this. She was trained her whole life for a situation like this. She did a three- quarter turn and punched the man in the stomach he bended over, which gave her a sliver of time to knee him in the balls to which he fell to his knees and dropped his gun. She picked it up and aimed it at him. _.45 what a pussy_ the club started to take notice and the cowards scampered.

The friends of the man tried to defend him from Kiara but she just fired two warning shots into the air. And chaos ensued, everyone was running. A couple of the hecklers tried to take down Kiara and punched her in the face dragged her outside of the club and kicked her in the stomach before someboy shot them all in the backs. Kiara was too tired to notice who had helped her when she heard a voice so familiar and angelic like.

"Meg hold on! PLEASE!" it was Castiel he had saved her.

As she slowly regained consciousness Castiel helped her to her feet, still badly injured she relied on him to help her walk, she was going to go back into the club when he stopped her.

"Cas what are you doing? I have to get my stuff, we have to help the others we can't just-"

"Listen Meg you're hurt I'm not having you die on my watch I'm taking you to a hospital" he said protectively as he walked her in the direction of his car and they sped away in the night.

 **YAAAAAAAS GUYS CH.4 PLEASE PLEASE PLEASE WRITE AND REVIEW MUCH LOVE LOVE LOVE GUYS**


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